Hydrochloric Acid → (3-Chloro-5-methoxyphenyl)methanol

関与物質

反応手順

To an ice-cold solution of 3-chloro-5-methoxybenzaldehyde (27 mmol, 4.60 g) in ethanol (90 ml) was added NaBH4 (30 mmol, 1.14 g) in one portion under stirring. After 0.5 h the mixture was allowed to reach room temperature and stirred for another 0.5 h. HCl (2 M, ˜25 ml)) was added slowly until no more hydrogen gas evolved, the resulting mixture was concentrated under reduced pressure and the residue separated between water and ether, the organic phase was washed with braine and dried (MgSO4). Filtration and evaporation of solvents afforded the title compound (4.53 g, 97%) as a white solid. The product was used without further purification in the next step. An analytically pure sample was obtained be means of flash chromatography (silica, hexane/ether grad.). 1H NMR (CDCl3, 500 MHz) δ 2.77 (br, 1H), 3.76 (s, 3H), 4.55 (s, 2H), 6.74 (s, 1H), 6.77 (s, 1H) and 6.88 (s, 1H).

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